(2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-(2H5)phenylpropanoic acid

• ChemBase ID: 175754
• Molecular Formular: C20H18ClNO6
• Molecular Mass: 403.81302
• Monoisotopic Mass: 403.08226498
• SMILES: [C@@H]1(OC(=O)c2c(C1)c(cc(c2O)C(=O)N[C@H](Cc1ccccc1)C(=O)O)Cl)C
• Canonical SMILES: C[C@H]1OC(=O)c2c(C1)c(Cl)cc(c2O)C(=O)N[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15-/m1/s1
• InChIKey: RWQKHEORZBHNRI-MEBBXXQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-(^2H₅)phenylpropanoic acid
• IUPAC Traditional name: (2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl]formamido}-3-(^2H₅)phenylpropanoic acid
• Synonyms: N-[[(3R)-5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-(phenyl-d5)alanine; (-)- N-[(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-(phenyl-d5)alanine; (R)-N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-benzo[c]pyran-7-yl)carbonyl]-3-(phenyl-d5)alanine; 3R,14S-Ochratoxin A-d5; NSC 201422-d5; NSC 221991-d5; Phe-OTA-d5; Phenylalanine-ochratoxin A-d5; Ochratoxin A-d5

Database IDs

• CAS Number: 666236-28-8
• PubChem SID: 164231664
• PubChem CID: 71751270

CALCULATED PROPERTIES

• Acid pKa: 3.1733449
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.307228
• LogD (pH = 7.4): 1.0533841
• Log P: 4.611056
• Molar Refractivity: 101.77 cm^3
• Polarizability: 38.782803 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O148492

Labelled Ochratoxin A (O148500). Ochratoxins are toxic metabolites from Aspergillus orchraceus.

REFERENCES

• Belli, N., et al.: Int. J. Food Microb., 96, 19 ( 2004), Pardo, E., et al.: Food Microb., 23, 35 (2006)